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Nouveaux types de sucres triazotés: triazènes et phénylimino‐2‐oxadiazoles‐1,3,4. Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Rachidzadeh Faranak
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590823
Subject(s) - chemistry , nitrogen atom , reagent , chloroform , nitrogen , tautomer , medicinal chemistry , tetrafluoroborate , stereochemistry , organic chemistry , group (periodic table) , catalysis , ionic liquid
Novel types of sugars bearing three nitrogen atoms: triazenes and 2‐phenylimino‐1, 3, 4‐oxadiazoles . A series of aminodeoxysugars treated with p ‐nitrobenzenediazonium tetrafluoroborate led to the corresponding triazenes, each of which in chloroform solution existing as an equilibrium between its two tautomeric forms. The free energy of activation of the exchange of the proton between the two nitrogen atoms has been estimated by variable temperature 1 H‐NMR. measurements. Each triazenylsugar gave on acetylation an unique positional isomer bearing its acyl group on the nitrogen atom directly attached to the glycosyl group. Phenylsemicarbazones of two keto‐sugars were oxidized with El Khadem's reagent (I 2 , HgO, MgO) to give the corresponding spiro ‐2‐phenylimino‐1, 3, 4‐oxadiazoles.